


A Successful Night

by thewinchesterlifestyle



Category: Supernatural
Genre: Bondage, Bottom Dean, Butt Plugs, Cheerleader Dean, Cock Slut Dean, Dean/OMCs - Freeform, Dirty Talk, Double Penetration, Double Penetration in One Hole, Double Penetration in Two Holes, Exhibitionism, Face-Fucking, Gangbang, HS AU, M/M, Multi, Name Calling, Public Sex, Riding, Rough Sex, Slut Dean, Spitroasting, Teen Dean, Underage - Freeform, Voyeurism, Wall Sex
Language: English
Status: Completed
Published: 2016-08-15
Updated: 2016-08-15
Packaged: 2018-08-09 00:35:44
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,350
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7780033
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: <blockquote class="userstuff">
              <p>Dean went to the party with only one thing in mind: getting laid.</p>
            </blockquote>





	A Successful Night

**Author's Note:**

> Written for prompt(s)
> 
> Dean: 16 yrs (hence the underage tag)  
> Guys in the basement: Various ages from 18+

Dean had gone to the party with one thing on his mind. Getting laid. He had slicked himself up, stretched his hole open until he could take one of his larger plugs, before he’d pressed it inside and dressed to go out. It had only taken two hours before he found himself in the basement with a group upperclassmen while the music from the party pounded above their heads.

“Let’s see that ass of yours, Winchester.” One of the guys, a member of the football team, leered as he looked at Dean with lust. “Want to see what I’m going to be fucking tonight.” The words had Dean’s cock aching with interest as he did exactly that.

Then hands touched him, moving over his bare skin once the clothing hit the floor and he was dragged down onto the lap of a classmate. “Little slut opened himself up for us.” Fingers tugged at Dean’s plug before it was popping free and being handed off to another guy. Dean didn’t care where it ended up as he found himself guided down onto a hard cock that stretched him and filled him up until he was completely seated.

“Come on. Ride him.” A voice from behind him spoke and Dean started to roll his hips, moaning at the feeling of the cock buried inside him. He could feel the eyes of those in the basement on him but it was the hot hands on his hips and the guy thrusting up into him that held his attention.

“Bet that ass can take two cocks at the same time.” The voice was rough and Dean could hear muffled movement behind him. “Sluts need cock. They need to be shown what they’re good for.”

“He’s so good at it.” Came a familiar voice, “I’ve had a go at him and Dean’s a regular whore for it. Loves nothing more than to be manhandled and pounded into until he’s hoarse from screaming.” Fingers tugged on Dean’s hair and he felt a hot mouth biting down on his neck until he whimpered at the combination of pain and pleasure his body was experiencing.

Dean felt a hand close down around his cock to hold off his orgasm as the guy under him came with a moan. The fingers at his hips had dug in hard enough to mark him with light bruises before he found himself being hauled off. He barely noticed the guy he’d been riding pulling off his condom as he was turned.

When the movements were done he found himself being guided down onto another cock, shoved into position so his head was angled towards another guy standing to the side, while yet another guy moved up behind him to start stretching him open further.

His mouth dropped open as he was fed another cock, Dean was sure the guy’s name was Jason or something with a J, while he whimpered around the heavy length. Instead of waiting for whoever was behind Dean to work him open Jason started to thrust inside Dean’s mouth. One set of hands held his body in position and the set belonging to Jason held his face in place.

Dean relaxed his throat as best he could, still feeling his eyes burning slightly, as he breathed through his nose and let the guy using his mouth fuck at the rhythm he’d chosen while Dean let himself be used.

“The very definition of a cockslut.” One of them spoke as the others in the basement watched Dean’s face being fucked by one of their classmates as another started to inch himself in alongside Will who Dean was sprawled out on.

“He took two.” Came a rough voice as Dean whimpered at the burn and stretch his ass was experiencing. He’d never been so full and the sounds he was trying to make vibrated against the cock in his mouth to earn a moan. It absolutely _burned_ being stretched so widely on two thick cocks. “I don’t think I’ve ever seen a greedier hole.”

Dean’s eyes snapped open when the two cocks buried inside his ass started to move together, dragging against his insides, while the voices in the room were muffled by the pounding of his heart. He was completely surrounded and full, stretched wide and held tight as the cock in his mouth shot down his throat.

He managed to swallow all of it as Jason pulled out, thumbing his slack lips, before one of the others in the basement decided to take their turn with the free hole. Dean’s moans were muffled by the new cock but this time the thrusting was far more greedy and rough as he struggled to control his gag-reflex to take it without gagging.

Dean choked several times, trying to relax, while pleasure twisted inside him.

It didn't take long before word had gotten around about what was happening in the basement and soon it wasn't just the upperclassmen from Dean's school that were waiting around for their turn.

The night was a blur of being used, passed around and teased, until he was a shaking mess and his voice was wrecked from moaning and begging for more. The last guy had him sprawled out on his back, arms stretched above his head with his hands tied and secured to the leg of a pool table, as he pounded into Dean’s puffy hole with filthy sounds filling the room.

His balls slapped against Dean’s ass, red from the spanking one guy had given him earlier, as he kept thrusting forward until he stilled as his orgasm finally washed over him. The guy pulled out, eyes dark and cheeks flushed, as he glanced down at Dean who blinked up at him as the guy pulled off the condom he’d been wearing. “Thanks for the fuck, Winchester.” Brown eyes moved from Dean to glance over at the only remaining guy in the basement. “Great party, Nick.”

Nick nodded as he walked over to free Dean from the pool table while his classmate tucked himself away before leaving.

Dean slowly sat up, moaning softly at the pain in his ass from the rough fucking he’d experienced most of the night, before he glanced over at Nick. He ignored the used condoms he could see and the turned over bottle of lube. “Shower is over there.” Nick jerked his head and watched Dean nod slowly as he stumbled in that direction.

There was a soft smile on Dean’s features as he felt how loose his muscles were. He enjoyed the well-used feeling his body was experiencing as he stepped under the hot spray and sighed out as it cascaded down his body as he reached for the soap to scrub himself clean.

He savored the hot water pounding down on him, lazily scrubbing himself and letting the water run over his body.

Once he was finished Dean reached out from behind the shower curtain to grab one of the towels. He slowly dried himself off and gingerly stepped out of the shower onto the soft rug. A sigh escaped and his eyes slid closed while he finished drying himself off before wrapping the towel around his waist.

“Nick?” he called out of the bathroom, glancing around the basement at the disaster. “Are you still down here?” Dean cleared his throat and ignored the scratchy sound of his voice from the rough fucking his throat had taken.

“Over here.” a voice called out.

Dean stepped out of the doorway and glanced to the right to see Nick picking up a few beer bottles to deposit in the trash. “Ummm.” He fidgeted slightly, “Did you see where my clothes went?”

Nick jerked his head in the direction of the couch and Dean nodded his thanks before he crossed the floor towards them. He could feel eyes on him, knew Nick was staring, but Dean had been naked in front of more people then he bothered to count. It came from thoroughly enjoying being fucked.

He didn’t care who looked at his naked body.

Dean picked up his shirt, checking it over to stains, until he heard Nick behind him. He continued looking over the shirt and grinned when Nick stepped closer to him. “Need something?” he turned his head and flashed a cheeky grin at the older teenager.

Instead of answering Nick turned him around and dragged Dean in for a kiss. A hand gripped the back of Dean’s head while their lips moved together. He leaned into it and blinked when Nick pulled back from him.

“Didn’t get enough of me earlier?” Dean stepped closer, mentally smirking at the look of open lust on Nick’s face. “Want to fuck me again?” he paused, “Want another shot at the _cheerleader_?”

Nick clenched his fist and instead of answering he yanked Dean back in for another kiss. He felt Dean melting into him and grinned into it as his hand snaked up to knot in Dean’s hair. “I prefer you all to myself.” He spoke when they broke apart and he tugged the towel from Dean’s waist.

The comment had Dean arching a brow and offering a cheeky smirk. Nick pulled his head back and started sucking a mark onto the exposed line of Dean’s neck.

“I’m _always_ available for a good fuck, Nick, you know that.” A tongue flicked out to lick over the mark, “Oh.” Dean tilted his head further and moaned when Nick’s other hand went down to tease his hardening cock. “ _Fuck_.” The word was hissed. “I really hope you’re not just going to tease me.” Nick bit him in response while giving Dean a few lazy strokes.

Dean’s fingers gripped the fabric of Nick’s shirt and his hips gave little abortive thrusts forward seeking friction. “I have every intention of being inside you.” He breathed out and Dean grinned in response. Nick’s hand fell away so he could look around. “Lube.” Nick muttered.

Slowly Dean drew back and wordlessly walked right towards the lube, still sticky from earlier. “This?” he waved the bottle before looking around. “Where did you—?” Nick took the bottle from him and started backing Dean towards the wall.

He pressed Dean back against the cool surface while Dean’s fingers went right for his pants and started to work them off. “Still loose?” Dean nodded before he went for Nick’s shirt and pulled it off.

Dean kept trying to hurry Nick along, insisting he was open enough but the older teenager wasn’t deterred until he’d pressed several lube slick fingers inside Dean. “Come on, Nick.” Dean clenched down on them and gripped Nick where he was holding onto him. “Put that cock into me. _Now_.”

Nick’s fingers withdrew and he hitched Dean higher so he could start to guide himself inside. It was harder with Dean pressed up against the wall, legs wrapped around him, but Nick finally buried himself inside. “ _Fuck_.” He hissed it out when Dean clenched down on him and tightened his legs.

They started to move with Nick thrusting up into Dean. Each upward thrust had Dean gripping him tighter. “Come on.” Dean goaded as his fingers knotted in Nick’s hair, “Make me feel it.” Nick pressed closer to him and dug his fingers in so he could start thrusting into Dean in earnest. “Yes. Oh fuck yes.”

Dean’s eyes slid closed in pleasure and after a while he reached between them to grip his cock. Nick’s cock continued to move inside him and the delicious burn of being stretched open on a cock had moans escaping him. He regretted letting Nick open him up more because he wanted more of a burn. He wanted to ride that edge of pain/pleasure right to orgasm.

Nick pressed their lips together again and Dean was more than happy to respond enthusiastically until Nick moved from Dean’s lips to suck a mark onto Dean’s neck.

“So beautiful.” The words almost missed Dean’s awareness as they were breathed so close to his skin but he heard them and blinked in surprise. “Dean.” Nick moaned his name and started to move faster, hips working.

Dean knew exactly how to get himself off quickly and it didn’t take much with Nick buried inside him. His ass clenched down on Nick’s cock and he came between them with a hoarse cry.

“Oh.” Nick only managed a few more thrusts before he came inside Dean. He could feel Dean’s legs slipping from his hips to lightly hook around the back of his thighs but he couldn’t be bothered to move back yet. Instead he pressed his face against Dean’s neck and breathed in.

“I don’t know about you but I would love to pass out about now. Hours of getting fucked and I’m actually a little tired.” Dean mumbled the words and tugged on Nick’s hair. “Let’s get cleaned up and you can show me where I can crash.” That got him a response and Nick’s cock slipped from him, trailing come. “Come on big guy.” He grinned lazily as they stumbled towards the bathroom. “I’ll let you use me however you want in the morning before I go.”

Dean ignored the feeling of come leaking from him as he walked back towards the bathroom. They cleaned up and Dean glanced around as Nick led him from the basement, up the stairs into the now empty house and then towards his room. Neither of them bothered with clothes and Dean willingly crawled under the covers of Nick’s bed with an exhausted sigh.

Every muscle in his body ached in a good way. He sighed and turned to shove his face against a pillow while Nick settled next to him. A few seconds passed before arms snaked out and dragged him back against a solid chest. “Mmmm.” Nick tangled their legs together and within seconds his breathing had evened out in sleep. Dean chuckled lowly and let himself drift off to sleep.

It had been a _very_ successful night and he was looking forward to a nice, hopefully rough, morning fuck before he went home.


End file.
